3-Bromo-4-oxo-4-phenylbutanoic acid → HCID 19603693, compound

HRID 1604650Notes

Reaction equation

HRID 1604650 reaction equation
[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([CH2:19][C:20](=[S:22])[NH2:21])=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].Br[CH:24]([C:29](=O)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH2:25][C:26]([OH:28])=[O:27]>C(OCC)(=O)C>[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([CH2:19][C:20]4[S:22][C:24]([CH2:25][C:26]([OH:28])=[O:27])=[C:29]([C:30]5[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=5)[N:21]=4)=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 2562953-Bromo-4-oxo-4-phenylbutanoic acidHCID 19603751HCID 19603751, compound

Product 1

HCID 19603693HCID 19603693, compoundYield 6.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-tert-butyl-2-[5-(thiocarbamoylmethyl)-benzofuran-2-yl]thiazole (740 mg) and 3-bromo-4-oxo-4-phenylbutanoic acid (600 mg) in ethyl acetate (8.0 ml) was heated under reflux for 13.5 hours. After being cooled, the resulting precipitates were collected by filtration and washed with ethyl acetate. The precipitates were dissolved in ethyl acetate, washed with aqueous sodium hydrogen carbonate solution and brine, dried over magnesium sulfate and concentrated under reduced pressure to give a mixture. The mixture was subjected to column chromatography on silica gel and eluted with a mixture of chloroform, methanol and ethyl acetate (20:1:1 to 20:1:2). The fractions containing object compound were combined and concentrated under reduced pressure to give 4-tert-butyl-2-{5-[(5-carboxymethyl-4-phenylthiazol-2-yl)methyl]benzofuran-2-yl}thiazole (72 mg).

Workup

  1. temperatureunder reflux for 13.5 hours
  2. temperatureAfter being cooled
  3. customthe resulting precipitates
  4. filtrationwere collected by filtration
  5. washwashed with ethyl acetate
  6. dissolutionThe precipitates were dissolved in ethyl acetate
  7. washwashed with aqueous sodium hydrogen carbonate solution and brine
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customto give a mixture
  11. washeluted with a mixture of chloroform, methanol and ethyl acetate (20:1:1 to 20:1:2)
  12. additionThe fractions containing object compound
  13. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3b8956297f6b41178643647f705e2124
Source dataset
uspto-grants-1999_11
Patent number
US05994378

Reaction notes

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